Compound of acetylaminosalicylic acid with aliphatic amines and process of making same



Patented Dec. 13, 1927.

UNITED STATES PATENT OFFICE.

GEORGE RAIZISS, OF PHILADELPHIA, DOWNE, PENNSYLVANIA, ASSIGNORS ILLINOIS, A CORPORATION OF ILLINOIS.

COMPOUND 01 ACETYLAMINOSALICYLIC ACID WITH ALIPHATIC AMINES AND PROCESS O1 MAKING SAME.

No Drawing.

. value as a bactericide.

General method.

Our improved products are obtained by treating an acetylaminosalicylic acid with an alcohol solution of an aliphatic amine.-

The mixture is added to ether and the precipitated material is filtered off and dried.

The obtained products are water soluble and usually quite well defined crystalline bodies possessing in vivo a marked bactericidal power and can be employed for many therapeutic purposes. In the follow ing examples, we describe products prepared from 5-acetylaminosalicyl1c acid which we have found should be of high grade and chemically pure in order to secure the best results.

Example 1.

3.5 grams of N-propylamine is dissolved in 50 c. c. of methyl alcohol. To this solution are graduall added 12 grams of 5'- acetylaminosalicylic acid. The entire liquid is slowly'filtered' into 800 c. c. of ether. On stirring a white crystalline substance precipitates. It is filtered ofit, washed several times with ether and dried. The prod- 0 uct is easily'sol'uble in water and alcohol.

This material is represented .by the formula COOH omcoHN K Ewample 2.

102 grams of pure 5-acetylaminosalicylic acid are dissolved in 1000 c. c. of methyl alcohol and filtered through a paper filter. 70 grams of pure hexamethylenetetramine are dissolved in 1000 c. c. of methyl alcohol and likewise filtered. The alcoholic solu-. tions of both products are mixed together. A thick, white, solid crystallizes. To this are added about 1500 c. c. of U. S. P. ether and the whole mixed thoroughly. The solid is separated from the ether and alcohol by Application filed October 15, 1925. Serial No. 62,856.

filtration by suction in porcelain or earthenware funnels. It is then thoroughly pressed out in the funnel and washed several times with U. S. P. ether. It is dried in vacuo over caustic soda for several days until it is perfectly dry'a-nd free from any odor of ether or alcohol. resented by the formula coon on CHzCOHN (03mm The scope of the invention should be determined by reference to the appended claims, said claims being construed as broad- 1y as possible, consistent with the state of the art. I

We claim as our invention:

1. As a new article of manufacture, an acetlaminosalicylic acid combined, with an alip atic amine.

2. As a new article of manufacture, 5- acet laminosalicylic acid combined with an alip atic amine.

3. As a. new article of manufacture, an acetylaminosalicylic acid combined with hexamethylenetetramine.

4. As a new article of manufacture, a compound formed. by combining 5-acetylaminosalicylic acid with hexamethylenetetramine. I

5. The improved method of preparing an article for the purpose described which consists in treating an acetylaminosalicylic acid with an alcoholic solution of an aliphatic amine and then precipitating the resulting product.

6. The improved process of reparing a body of the class described whic consists in treating an acet laminosalicylic acid with a methyl alcoho solution of an aliphatic amine and then precipitating the product.

7. The improved process of preparing a This compound is rep body of the class described which consists in treating 5-acetylaminosalicylic acid with a methyl alcohol solution of an aliphatic amine and then precipitating the product with ether.

8. The improvement in the method of preparing a product of the class described which consists in preparing a solution of 5- ticetylaminosalicylic acid in methyl alcohol, mixing therewith a methyl alcohol solution 10 of hemmethylenetetramine, Washing and drying.

GEORGE W. RAIZISS.

AVENIR PROSKUURIAKOFF. 

